Sodium Hydroxide → 3-Chloro-5-fluorobenzyl 4-(4-(1-((pivaloyloxy)methyl)-1H-1,2,3-triazol-4-yl)butanamido)piperidine-1-carboxylate

HRID 1480441Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1480441
[C:1]([O:7][CH2:8][N:9]1[CH:13]=[C:12]([CH2:14][CH2:15][CH2:16][C:17](=[O:25])[NH:18][CH:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)[N:11]=[N:10]1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[C:26](=O)([O:37]N1C(=O)CCC1=O)[O:27][CH2:28][C:29]1[CH:34]=[C:33]([F:35])[CH:32]=[C:31]([Cl:36])[CH:30]=1.[OH-].[Na+]>C(Cl)Cl>[C:1]([O:7][CH2:8][N:9]1[CH:13]=[C:12]([CH2:14][CH2:15][CH2:16][C:17]([NH:18][CH:19]2[CH2:20][CH2:21][N:22]([C:26]([O:27][CH2:28][C:29]3[CH:34]=[C:33]([F:35])[CH:32]=[C:31]([Cl:36])[CH:30]=3)=[O:37])[CH2:23][CH2:24]2)=[O:25])[N:11]=[N:10]1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]

Komponenten

5

Edukt 3

HCID 14798Sodium Hydroxide2×HCID 86722666HCID 86722666, VerbindungHCID 867226683-Chloro-5-fluorobenzyl 2,5-dioxopyrrolidin-1-yl carbonate

Produkt 1

HCID 867226673-Chloro-5-fluorobenzyl 4-(4-(1-((pivaloyloxy)methyl)-1H-1,2,3-triazol-4-yl)butanamido)piperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel3×

Versuchsvorschrift

To a stirred suspension of (4-(4-oxo-4-(piperidin-4-ylamino)butyl)-1H-1,2,3-triazol-1-yl)methyl pivalate (step 5) (150 mg, 0.387 mmol) and 3-chloro-5-fluorobenzyl 2,5-dioxopyrrolidin-1-yl carbonate (117 mg, 0.387 mmol) in DCM (5 mL) was added NaOH (1.547 mL, 1.547 mmol) with stirring at RT and the mixture was stirred at RT for 18 hrs. A further 5 ml DCM was added followed by 1M NaOH (1 ml). The reaction mixture was diluted with DCM (30 ml) and the organic portion was dried over MgSO4, filtered and concentrated under reduced pressure to afford the title product;

Aufarbeitung

  1. stirringthe mixture was stirred at RT for 18 hrs
  2. dry with materialthe organic portion was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-7123f637e6a049abad14d7391e2f9447
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09409895B2

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